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1,4-Dioxane → 7-Chloro-3-(2,4-difluorophenyl)thieno[3,2-b]pyridine

HRID 593770
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 593770
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][C:10]([Cl:11])=[C:5]2[S:4][CH:3]=1.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1B(O)O.O1CCOCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:11][C:10]1[CH:9]=[CH:8][N:7]=[C:6]2[C:2]([C:16]3[CH:15]=[CH:14][C:13]([F:12])=[CH:18][C:17]=3[F:19])=[CH:3][S:4][C:5]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 27343342,4-Difluorophenylboronic acidHCID 867304243-Bromo-7-chlorothieno[3,2-b]pyridine

Produkt 1

HCID 867304267-Chloro-3-(2,4-difluorophenyl)thieno[3,2-b]pyridineAusbeute 360,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807
HCID 178418807, Verbindung
Katalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A vessel capable of sealing was charged with a mixture of 3-bromo-7-chlorothieno[3,2-b]pyridine (110 mg, 0.443 mmol), 2,4-difluorophenylboronic acid (84 mg, 0.531 mmol), PdCl2(dppf)-CH2Cl2 adduct (18.1 mg, 0.022 mmol), dioxane (3 mL), and a 2.0 M aqueous solution of K3PO4 (0.66 mL, 1.328 mmol) and was purged with nitrogen for 10 min. The vessel was sealed and heated at 90° C. for 3 hours. Upon cooling, the reaction mixture was diluted with water and extracted with CH2Cl2. The combined organics were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by BIOTAGE® eluting with 30%-60% CH2Cl2/hexanes at 30 mL/min. Concentration of appropriate fractions provided the title compound (450 mg, 49% yield) as a white powder. LC/MS: Example 102A @ 3.60 min (RT) (Condition G). MS (ES): m/z=282.02/284.02, [M+H]+.

Aufarbeitung

  1. customThe vessel was sealed
  2. temperatureUpon cooling
  3. extractionextracted with CH2Cl2
  4. washThe combined organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by BIOTAGE®
  8. washeluting with 30%-60% CH2Cl2/hexanes at 30 mL/min

Quellen und Nachweise

ORD-Eintrag
ord-fb3950441ba643aea54b3897651b02f0
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242967B2

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